EP0930022A2 - Use of carotinoid aggregates as colourants - Google Patents
Use of carotinoid aggregates as colourants Download PDFInfo
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- EP0930022A2 EP0930022A2 EP98122311A EP98122311A EP0930022A2 EP 0930022 A2 EP0930022 A2 EP 0930022A2 EP 98122311 A EP98122311 A EP 98122311A EP 98122311 A EP98122311 A EP 98122311A EP 0930022 A2 EP0930022 A2 EP 0930022A2
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- aggregates
- carotenoid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/58—Colouring agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
Definitions
- the invention relates to the use of carotenoid aggregates as a colorant.
- Carotenoids are a widely used class of dyes in nature, which are already in various forms for coloring food, Cosmetics and non-food items are used. However, the possible applications are severely limited that the group of carotenoids is generally very is sensitive to light and oxygen. In practice, therefore preparations colored with carotenoids, for example by degassing or by storing in opaque containers protected from light and oxygen.
- Carotenoid aggregates can be produced in this way, for example that a solution of a carotenoid in a water-miscible, organic solvents such as Isopropanol, Ethanol, acetone or tetrahydrofuran mixed with water.
- a solution of a carotenoid in a water-miscible, organic solvents such as Isopropanol, Ethanol, acetone or tetrahydrofuran mixed with water.
- H-aggregates are understood as a "card game-like" Stacking of the poly-chains (card-stack aggregate), which are in the UV / Vis spectrum due to the appearance of a new, in comparison to absorb the monomeric forms hypsochromically shifted Characterize a band in the range between 320 and 400 nm leaves.
- J-aggregates represent a linear head-tail Linking (head-tail aggregate) of the polyenes, the one bathochromic shift in UV absorption.
- the Carotenoid aggregates excellent for coloring food, cosmetic and pharmaceutical preparations as well as non-food objects, in particular of those preparations in which the dye is exposed to light.
- the carotenoid aggregates mentioned at the beginning are used as coloring agents preferably the H and / or J aggregates, particularly preferably uses the J aggregates.
- the carotenoids, in the form of aggregates as colorants can be used are the known, natural or synthetic representatives of this class, e.g. ⁇ -carotene, Lycopene, bixin, zeaxanthin, cryptoxanthin, citranaxanthin, Lutein, canthaxanthin, astaxanthin. Be particularly preferred the now technically easily accessible representatives such as ⁇ -carotene, astaxanthin or lycopene, especially astaxanthin and / or lycopene used.
- Protective colloids are, for example, gelatin, fish gelatin, Starch, dextrin, plant proteins, pectin, gum arabic, Casein, caseinate or mixtures thereof are used. But it can also polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, Carboxymethyl cellulose, hydroxypropyl cellulose and alginates be used. For more details, see R.A. Morton, Fat Soluble Vitamins, Intern. Encyclopedia of Food and Nutrition, Vol. 9, Pergamon Press 1970, pp. 128-131.
- a plasticizer to the colloid, such as sugar or sugar alcohols, e.g. Sucrose, glucose, Lactose, invert sugar, sorbitol, mannitol or glycerin.
- sugar or sugar alcohols e.g. Sucrose, glucose, Lactose, invert sugar, sorbitol, mannitol or glycerin.
- the amounts of protective colloid, plasticizer and carotenoid aggregate are generally chosen so that an end product is obtained is between 0.1 and 100 ppm, preferably between 0.5 and 50 ppm, particularly preferably 1 to 20 ppm carotenoid, preferred Astaxanthin or lycopene, 20 to 200 ppm of a protective colloid, 20 to 200 ppm of a plasticizer, all ppm data based on the total mass of the finished preparation, and if appropriate contains small amounts of a stabilizer.
- stabilizers such as ⁇ -tocopherol, t-butyl-hydroxy-toluene, t-butylhydroxyanisole, ascorbic acid or Add ethoxyguin.
- emulsifiers for example, ascorbyl palmitate, polyglycerol fatty acid esters, Sorbitan fatty acid esters, propylene glycol fatty acid esters or lecithin in a concentration of 0 to 200% by weight, preferably 10 to 150% by weight, particularly preferred 15 to 80% by weight, based on the carotenoid, can be used.
- Carotenoid aggregate a physiologically approved oil such as Sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil and esters of medium-chain vegetable fatty acids in a concentration of 0 to 500% by weight, preferably 10 to 300% by weight, particularly preferably 20 to 100% by weight, based on the Carotenoid to use.
- a physiologically approved oil such as Sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil and esters of medium-chain vegetable fatty acids in a concentration of 0 to 500% by weight, preferably 10 to 300% by weight, particularly preferably 20 to 100% by weight, based on the Carotenoid to use.
- the present invention also relates to foods which Carotenoid aggregates, in particular aggregates of astaxanthin and / or Lycopene in amounts of 0.1 to 100 ppm, preferably 0.5 to 50 ppm, particularly preferably 1 to 20 ppm (based on the total amount the preparation) included.
- Food can include about dairy products, fats, such as. Margarine and preferably around drinks, for example around Trade "soft drinks”.
- the colored drinks can be both transparent as well as cloudy, i.e. opaque preparations act.
- the use of the carotenoid aggregates is preferred for coloring transparent beverage preparations.
- the invention Carotenoid aggregates can be both in the form an emulsion or a suspension, as dry powder or Work the solubilizate into the drink.
- the present invention furthermore relates to cosmetic and pharmaceutical preparations, the 0.1 to 100 ppm, preferred 0.5 to 50 ppm, particularly preferably 1 to 20 ppm carotenoid aggregates, based on the total amount of cosmetic and pharmaceutical preparation included.
- compositions are in the Usually based on a carrier that has at least one oil phase contains.
- preparations are also aqueous only Basis when using compounds with hydrophilic substituents possible. Accordingly, oils, oil-in-water and water-in-oil emulsions, Creams and pastes, lip protection stick masses or fat-free Gels into consideration.
- Such cosmetic or pharmaceutical preparations can accordingly be in liquid, pasty or solid form, for example as water-in-oil creams, oil-in-water creams and lotions, Aerosol foam creams, gels, oils, fat sticks, powders, sprays or alcoholic water lotions.
- Common oil components in cosmetics are, for example Paraffin oil, glyceryl stearate, isopropyl myristate, diisopropyl adipate, 2-ethylhexanoic acid, cetylstearyl ester, hydrogenated polyisobutene, Vaseline, caprylic acid / capric acid triglycerides, microcrystalline Wax, lanolin and stearic acid.
- Usual cosmetic adjuvants considered as additives can come are e.g. Co-emulsifiers, fats and waxes, Stabilizers, thickeners, biogenic agents, film formers, Fragrances, additional dyes, pearlescent agents, Preservatives, pigments, electrolytes (e.g. magnesium sulfate) and pH regulators.
- Preferred co-emulsifiers are well-known W / O and also O / W emulsifiers such as Polyglycerol esters, sorbitan esters or partially esterified glycerides in Consideration.
- Typical examples of fats are glycerides; as waxes include Beeswax, paraffin wax or micro waxes if necessary in combination with hydrophilic waxes.
- Stabilizers can contain metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate can be used.
- Suitable thickeners are, for example, crosslinked polyacrylic acids and their derivatives, polysaccharides, in particular Xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also fatty alcohols, Monoglycerides and fatty acids, polyacrylates, polyvinyl alcohol and Polyvinyl pyrrolidone.
- Biogenic active ingredients are, for example Plant extracts, protein hydrolyzates and vitamin complexes too understand.
- Common film formers are, for example, hydrocolloids such as chitosan, microcrystalline chitosan or quaternized Chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, Polymers of the acrylic acid series, quaternary Cellulose derivatives and similar compounds.
- a preservative are suitable, for example, formaldehyde solution, p-hydroxybenzoate or sorbic acid.
- pearlescent agents are: Glycol distearic acid esters such as ethylene glycol distearate, however also fatty acids and fatty acid monoglycol esters into consideration.
- dyes used in addition to the carotenoid aggregates can use those approved and approved for cosmetic purposes Substances are used, such as in the Publication "Cosmetic Dyes” of the Dye Coimmission the German Research Foundation, published by the publisher Chemie, Weinheim, 1984. These dyes are usually in a concentration of 0.001 to 0.1% by weight, based on the entire mixture used.
- the total proportion of auxiliaries and additives can be 1 to 80, preferably 6 to 40% by weight and the non-aqueous portion ("active substance") 20 to 80, preferably 30 to 70 wt .-% based on the total amount of preparation - amount.
- the manufacture of the Preparation can be carried out in a manner known per se, i.e. for example by hot, cold, hot-hot / cold or PIT emulsification.
- Preferred cosmetic or pharmaceutical preparations are for example, transparent formulations in the form of more transparent Emulsions, solubilisates, gels or alcoholic-aqueous Lotions.
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Abstract
Description
Die Erfindung betrifft die Verwendung von Carotinoid-Aggregaten als Färbemittel.The invention relates to the use of carotenoid aggregates as a colorant.
Carotinoide sind eine in der Natur weit verbreitete Farbstoffklasse, die bereits in vielfältiger Form zum Färben von Lebensmitteln, Kosmetika und Non-Food-Artikeln eingesetzt werden. Die Anwendungsmöglichkeiten sind allerdings dadurch stark eingeschränkt, daß die Stoffgruppe der Carotinoide generell sehr licht- und sauerstoffempfindlich ist. In der Praxis müssen daher mit Carotinoiden gefärbte Zubereitungen beispielsweise durch Entgasen oder durch Aufbewahrung in lichtundurchlässigen Gefässen vor Licht und Sauerstoff geschützt werden.Carotenoids are a widely used class of dyes in nature, which are already in various forms for coloring food, Cosmetics and non-food items are used. However, the possible applications are severely limited that the group of carotenoids is generally very is sensitive to light and oxygen. In practice, therefore preparations colored with carotenoids, for example by degassing or by storing in opaque containers protected from light and oxygen.
Es war daher die Aufgabe, stabile Carotinoid-Formen als Färbemittel bereitzustellen, die die oben genannten Nachteile nicht aufweisen.It was therefore the task of using stable carotenoid forms as colorants to provide, which do not have the disadvantages mentioned above exhibit.
Diese Aufgabe wurde erfindungsgemäß gelöst durch die Verwendung von Carotinoid-Aggregaten als Färbemittel.This object has been achieved according to the invention through the use of carotenoid aggregates as colorants.
Die Aggregation von Carotinoiden ist ein in der Literatur bereits bekanntes und in zahlreichen Publikationen beschriebenes Phänomen [P. Song, T. A. Moore, Photochemistry and Photobiology, 19, 435-441 (1974); A. V. Ruban, P. Horton, A. J. Young, J. Photochem. Photobiol. B: Biol., 21, 229-234 (1993); U. R. Salares, H. H. Young, P. R. Carey, H. J. Bernstein, Journal of Raman Spectroscopy, 6(6), 282-288 (1977)].The aggregation of carotenoids is already one in the literature well-known phenomenon described in numerous publications [P. Song, T.A. Moore, Photochemistry and Photobiology, 19, 435-441 (1974); A.V. Ruban, P. Horton, A.J. Young, J. Photochem. Photobiol. B: Biol., 21, 229-234 (1993); U. R. Salares, H.H. Young, P.R. Carey, H.J. Bernstein, Journal of Raman Spectroscopy, 6 (6), 282-288 (1977)].
Carotinoid-Aggregate können beispielsweise dadurch erzeugt werden, daß man eine Lösung eines Carotinoids in einem wassermischbaren, organischen Lösungsmittel wie z.B. Isopropanol, Ethanol, Aceton oder Tetrahydrofuran mit Wasser vermischt.Carotenoid aggregates can be produced in this way, for example that a solution of a carotenoid in a water-miscible, organic solvents such as Isopropanol, Ethanol, acetone or tetrahydrofuran mixed with water.
So können, wie in der oben genannten Literatur beschrieben, bei Wahl der richtigen Mengenverhältnisse von Wasser und organischem Lösungsmittel entweder sogenannte H- oder J-Aggregate erzeugt werden.So, as described in the above literature, at Choosing the right proportions of water and organic Solvent generated either so-called H or J aggregates become.
Unter H-Aggregaten versteht man eine "kartenspielähnliche" Stapelung der Polyenketten (card-stack aggregate), die sich im UV/Vis-Spektrum durch das Auftreten einer neuen, im Vergleich zur Absorption der monomer vorliegenden Formen hypsochrom verschobenen Bande im Bereich zwischen 320 und 400 nm charakterisieren laßt. J-Aggregate dagegen stellen eine lineare Kopf-Schwanz Verknüpfung (head-tail aggregate) der Polyene dar, die eine bathochrome Verschiebung der UV-Absorption bewirkt.H-aggregates are understood as a "card game-like" Stacking of the poly-chains (card-stack aggregate), which are in the UV / Vis spectrum due to the appearance of a new, in comparison to absorb the monomeric forms hypsochromically shifted Characterize a band in the range between 320 and 400 nm leaves. J-aggregates, on the other hand, represent a linear head-tail Linking (head-tail aggregate) of the polyenes, the one bathochromic shift in UV absorption.
Diese Aggregate sind somit im Farbton von dem monomer gelösten Carotinoid verschieden und können sowohl visuell an dieser Farbverschiebung als auch UV/Vis-spektroskopisch erkannt werden.The color of these aggregates is thus detached from the monomer Carotenoid is different and can be seen both visually at this color shift as well as UV / Vis spectroscopic detection.
Es wurde nun überraschenderweise gefunden, daß diese CarotinoidAggregate bei Bestrahlung mit Licht, beispielsweise mit einer Xenonlampe, eine wesentlich höhere Lichtstabilität aufweisen als die in monomerer Form vorliegenden Carotinoide.It has now surprisingly been found that these carotenoid aggregates when irradiated with light, for example with a Xenon lamp, have a much higher light stability than the carotenoids present in monomeric form.
Aufgrund dieser ausgezeichneten Photostabilität eignen sich die Carotinoid-Aggregate hervorragend zum Färben von Lebensmitteln, kosmetischen und pharmazeutischen Zubereitungen sowie von Non-Food-Objekten, insbesondere von solchen Zubereitungen, bei denen der Farbstoff dem Licht ausgesetzt ist.Because of this excellent photo stability, the Carotenoid aggregates excellent for coloring food, cosmetic and pharmaceutical preparations as well as non-food objects, in particular of those preparations in which the dye is exposed to light.
Als Färbemittel werden von den eingangs genannten CarotinoidAggregaten bevorzugt die H- und/oder J-Aggregate, besonders bevorzugt die J-Aggregate verwendet.The carotenoid aggregates mentioned at the beginning are used as coloring agents preferably the H and / or J aggregates, particularly preferably uses the J aggregates.
Die Carotinoide, die in Form von Aggregaten als Färbemittel eingesetzt werden können, sind die bekannten, natürlichen oder synthetischen Vertreter dieser Klasse, wie z.B. β-Carotin, Lycopin, Bixin, Zeaxanthin, Cryptoxanthin, Citranaxanthin, Lutein, Canthaxanthin, Astaxanthin. Besonders bevorzugt werden die mittlerweile auch technisch gut zugänglichen Vertreter wie β-Carotin, Astaxanthin oder Lycopin, insbesondere Astaxanthin und/oder Lycopin verwendet.The carotenoids, in the form of aggregates as colorants can be used are the known, natural or synthetic representatives of this class, e.g. β-carotene, Lycopene, bixin, zeaxanthin, cryptoxanthin, citranaxanthin, Lutein, canthaxanthin, astaxanthin. Be particularly preferred the now technically easily accessible representatives such as β-carotene, astaxanthin or lycopene, especially astaxanthin and / or lycopene used.
Bei der erfindungsgemäßen Verwendung der Carotinoid-Aggregate als Färbemittel können diese allein oder vorteilhafterweise in Gegenwart von Schutzkolloiden eingesetzt werden.When using the carotenoid aggregates according to the invention as Colorants can do this alone or advantageously in the presence of protective colloids.
Als Schutzkolloide werden beispielsweise Gelatine, Fischgelatine, Stärke, Dextrin, Pflanzenproteine, Pektin, Gummi-Arabikum, Kasein, Kaseinat oder Mischungen davon verwendet. Es können aber auch Polyvinylalkohol, Polyvinylpyrrolidon, Methylcellulose, Carboxymethylcellulose, Hydroxypropylcellulose und Alginate eingesetzt werden. Bezüglich näherer Einzelheiten wird auf R.A. Morton, Fat Soluble Vitamins, Intern. Encyclopedia of Food and Nutrition, Bd.9, Pergamon Press 1970, S. 128-131, verwiesen. Protective colloids are, for example, gelatin, fish gelatin, Starch, dextrin, plant proteins, pectin, gum arabic, Casein, caseinate or mixtures thereof are used. But it can also polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, Carboxymethyl cellulose, hydroxypropyl cellulose and alginates be used. For more details, see R.A. Morton, Fat Soluble Vitamins, Intern. Encyclopedia of Food and Nutrition, Vol. 9, Pergamon Press 1970, pp. 128-131.
Zur Erhöhung der mechanischen Stabilität der Carotinoid-Formulierung kann es zweckmäßig sein, dem Kolloid einen Weichmacher zuzusetzen, wie Zucker oder Zuckeralkohole, z.B. Saccharose, Glucose, Lactose, Invertzucker, Sorbit, Mannit oder Glycerin.To increase the mechanical stability of the carotenoid formulation it may be useful to add a plasticizer to the colloid, such as sugar or sugar alcohols, e.g. Sucrose, glucose, Lactose, invert sugar, sorbitol, mannitol or glycerin.
Die Mengen an Schutzkolloid, Weichmacher und Carotinoid-Aggregat werden im allgemeinen so gewählt, daß ein Endprodukt erhalten wird, das zwischen 0,1 und 100 ppm, bevorzugt zwischen 0,5 und 50 ppm, besonders bevorzugt 1 bis 20 ppm Carotinoid, bevorzugt Astaxanthin oder Lycopin, 20 bis 200 ppm eines Schutzkolloids, 20 bis 200 ppm eines Weichmachers, alle ppm-Angaben bezogen auf die Gesamtmasse der fertigen Zubereitung, sowie gegebenenfalls geringe Mengen eines Stabilisators enthält.The amounts of protective colloid, plasticizer and carotenoid aggregate are generally chosen so that an end product is obtained is between 0.1 and 100 ppm, preferably between 0.5 and 50 ppm, particularly preferably 1 to 20 ppm carotenoid, preferred Astaxanthin or lycopene, 20 to 200 ppm of a protective colloid, 20 to 200 ppm of a plasticizer, all ppm data based on the total mass of the finished preparation, and if appropriate contains small amounts of a stabilizer.
Zur Erhöhung der Stabilität der Carotinoide gegen oxidativen Abbau ist es vorteilhaft, Stabilisatoren wie α-Tocopherol, t-Butyl-hydroxy-toluol, t-Butylhydroxyanisol, Ascorbinsäure oder Ethoxyguin zuzusetzen.To increase the stability of the carotenoids against oxidative Degradation, it is advantageous to use stabilizers such as α-tocopherol, t-butyl-hydroxy-toluene, t-butylhydroxyanisole, ascorbic acid or Add ethoxyguin.
Als Emulgatoren können beispielsweise Ascorbylpalmitat, Polyglycerin-Fettsäureester, Sorbitan-Fettsäureester, PropylenglycolFettsäureester oder Lecithin in einer Konzentration von 0 bis 200 Gew.%, vorzugsweise 10 bis 150 Gew.%, besonders bevorzugt 15 bis 80 Gew.%, bezogen auf das Carotinoid, verwendet werden.As emulsifiers, for example, ascorbyl palmitate, polyglycerol fatty acid esters, Sorbitan fatty acid esters, propylene glycol fatty acid esters or lecithin in a concentration of 0 to 200% by weight, preferably 10 to 150% by weight, particularly preferred 15 to 80% by weight, based on the carotenoid, can be used.
Unter Umständen kann es auch vorteilhaft sein, zusätzlich zum Carotinoid-Aggregat ein physiologisch zugelassenes ÖL wie beispielsweise Sesamöl, Maiskeimöl, Baumwollsaatöl, Sojabohnenöl oder Erdnußöl sowie Ester mittelkettiger pflanzlicher Fettsäuren in einer Konzentration von 0 bis 500 Gew.%, vorzugsweise 10 bis 300 Gew.%, besonders bevorzugt 20 bis 100 Gew.%, bezogen auf das Carotinoid, zu verwenden.It may also be advantageous in addition to Carotenoid aggregate a physiologically approved oil such as Sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil and esters of medium-chain vegetable fatty acids in a concentration of 0 to 500% by weight, preferably 10 to 300% by weight, particularly preferably 20 to 100% by weight, based on the Carotenoid to use.
Gegenstand der vorliegenden Erfindung sind auch Lebensmittel, die Carotinoid-Aggregate, insbesondere Aggregate von Astaxanthin und/oder Lycopin in Mengen von 0,1 bis 100 ppm, bevorzugt 0,5 bis 50 ppm, besonders bevorzugt 1 bis 20 ppm (bezogen auf die Gesamtmenge der Zubereitung) enthalten.The present invention also relates to foods which Carotenoid aggregates, in particular aggregates of astaxanthin and / or Lycopene in amounts of 0.1 to 100 ppm, preferably 0.5 to 50 ppm, particularly preferably 1 to 20 ppm (based on the total amount the preparation) included.
Bei den Lebensmitteln kann es sich u.a. um Milchprodukte, Fette, wie z.B. Margarine sowie bevorzugt um Getränke, beispielsweise um "Soft-Drinks" handeln.Food can include about dairy products, fats, such as. Margarine and preferably around drinks, for example around Trade "soft drinks".
Es kann sich bei den gefärbten Getränken sowohl um transparente als auch um trübe, d.h. lichtundurchlässige Zubereitungen handeln. Bevorzugt ist die Verwendung der Carotinoid-Aggregate zur Färbung transparenter Getränkezubereitungen. Die erfindungsgemäßen Carotinoid-Aggregate lassen sich dabei sowohl in Form einer Emulsion oder einer Suspension, als Trockenpulver oder Solubilisat in das Getränk einarbeiten.The colored drinks can be both transparent as well as cloudy, i.e. opaque preparations act. The use of the carotenoid aggregates is preferred for coloring transparent beverage preparations. The invention Carotenoid aggregates can be both in the form an emulsion or a suspension, as dry powder or Work the solubilizate into the drink.
Bei der Verwendung der Carotinoid-Aggregate in Lebensmitteln können vorher die nicht für Lebensmittel zugelassenen organischen Lösungsmittel, wie beispielsweise Aceton oder THF, schonend abdestilliert werden, ohne daß es zu einer Änderung der Aggregatform kommt.When using the carotenoid aggregates in food can previously be the organic not approved for food Solvents such as acetone or THF are carefully distilled off without changing the shape of the aggregate is coming.
Gegenstand der vorliegenden Erfindung sind weiterhin kosmetische und pharmazeutische Zubereitungen, die 0,1 bis 100 ppm, bevorzugt 0,5 bis 50 ppm, besonders bevorzugt 1 bis 20 ppm Carotinoid-Aggregate, bezogen auf die Gesamtmenge der kosmetischen und pharmazeutischen Zubereitung enthalten.The present invention furthermore relates to cosmetic and pharmaceutical preparations, the 0.1 to 100 ppm, preferred 0.5 to 50 ppm, particularly preferably 1 to 20 ppm carotenoid aggregates, based on the total amount of cosmetic and pharmaceutical preparation included.
Diese kosmetischen und pharmazeutischen Zubereitungen sind in der Regel auf der Basis eines Trägers, der mindestens eine Ölphase enthält. Es sind aber auch Zubereitungen allein auf wäßriger Basis bei Verwendung von Verbindungen mit hydrophilen Substituenten möglich. Demgemäß kommen Öle, Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, Cremes und Pasten, Lippenschutzstiftmassen oder fettfreie Gele in Betracht.These cosmetic and pharmaceutical preparations are in the Usually based on a carrier that has at least one oil phase contains. However, preparations are also aqueous only Basis when using compounds with hydrophilic substituents possible. Accordingly, oils, oil-in-water and water-in-oil emulsions, Creams and pastes, lip protection stick masses or fat-free Gels into consideration.
Solche kosmetischen oder pharmazeutischen Präparate können demgemäß in flüssiger, pastöser oder fester Form vorliegen, beispielsweise als Wasser-in-Öl-Cremes, Öl-in-Wasser-Cremes und -Lotionen, Aerosol-Schaumcremes, Gele, Öle, Fettstifte, Puder, Sprays oder alkoholisch-wäßrige Lotionen.Such cosmetic or pharmaceutical preparations can accordingly are in liquid, pasty or solid form, for example as water-in-oil creams, oil-in-water creams and lotions, Aerosol foam creams, gels, oils, fat sticks, powders, sprays or alcoholic water lotions.
Übliche Ölkomponenten in der Kosmetik sind beispielsweise Paraffinöl, Glycerylstearat, Isopropylmyristat, Diisopropyladipat, 2-Ethylhexansäurecetylstearylester, hydriertes Polyisobuten, Vaseline, Caprylsäure/Caprinsäure-Triglyceride, mikrokristallines Wachs, Lanolin und Stearinsäure.Common oil components in cosmetics are, for example Paraffin oil, glyceryl stearate, isopropyl myristate, diisopropyl adipate, 2-ethylhexanoic acid, cetylstearyl ester, hydrogenated polyisobutene, Vaseline, caprylic acid / capric acid triglycerides, microcrystalline Wax, lanolin and stearic acid.
Übliche kosmetische Hilfsstoffe, die als Zusätze in Betracht kommen können, sind z.B. Co-Emulgatoren, Fette und Wachse, Stabilisatoren, Verdickungsmittel, biogene Wirkstoffe, Filmbildner, Duftstoffe, zusätzliche Farbstoffe, Perlglanzmittel, Konservierungsmittel, Pigmente, Elektrolyte (z.B. Magnesiumsulfat) und pH-Regulatoren. Als Co-Emulgatoren kommen vorzugsweise bekannte W/O- und daneben auch O/W-Emulgatoren wie etwa Polyglycerinester, Sorbitanester oder teilveresterte Glyceride in Betracht. Typische Beispiele für Fette sind Glyceride; als Wachse sind u.a. Bienenwachs, Paraffinwachs oder Mikrowachse gegebenenfalls in Kombination mit hydrophilen Wachsen zu nennen. Als Stabilisatoren können Metallsalze von Fettsäuren wie z.B. Magnesium-, Aluminium- und/oder Zinkstearat eingesetzt werden. Geeignete Verdickungsmittel sind beispielsweise vernetzte Polyacrylsäuren und deren Derivate, Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcellulose und Hydroxyethylcellulose, ferner Fettalkohole, Monoglyceride und Fettsäuren, Polyacrylate, Polyvinylalkohol und Polyvinylpyrrolidon. Unter biogenen Wirkstoffen sind beispielsweise Pflanzenextrakte, Eiweißhydrolysate und Vitaminkomplexe zu verstehen. Gebräuchliche Filmbildner sind beispielsweise Hydrocolloide wie Chitosan, mikrokristallines Chitosan oder quaterniertes Chitosan, Polyvinylpyrrolidon, Vinylpyrrolidon-Vinylacetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Cellulose-Derivate und ähnliche Verbindungen. Als Konservierungsmittel eignen sich beispielsweise Formaldehydlösung, p-Hydroxybenzoat oder Sorbinsäure. Als Perlglanzmittel kommen beispielsweise Glycoldistearinsäureester wie Ethylenglycoldistearat, aber auch Fettsäuren und Fettsäuremonoglycolester in Betracht. Als zusätzlich zu den Carotinoid-Aggregaten verwendete Farbstoffe können die für kosmetische Zwecke geeigneten und zugelassenen Substanzen verwendet werden, wie sie beispielsweise in der Publikation "Kosmetische Färbemittel" der Farbstoffkoimmission der Deutschen Forschungsgemeinschaft, veröffentlicht im Verlag Chemie, Weinheim, 1984, zusammengestellt sind. Diese Farbstoffe werden üblicherweise in Konzentration von 0,001 bis 0,1 Gew. -%, bezogen auf die gesamte Mischung, eingesetzt.Usual cosmetic adjuvants considered as additives can come are e.g. Co-emulsifiers, fats and waxes, Stabilizers, thickeners, biogenic agents, film formers, Fragrances, additional dyes, pearlescent agents, Preservatives, pigments, electrolytes (e.g. magnesium sulfate) and pH regulators. Preferred co-emulsifiers are well-known W / O and also O / W emulsifiers such as Polyglycerol esters, sorbitan esters or partially esterified glycerides in Consideration. Typical examples of fats are glycerides; as waxes include Beeswax, paraffin wax or micro waxes if necessary in combination with hydrophilic waxes. As Stabilizers can contain metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate can be used. Suitable thickeners are, for example, crosslinked polyacrylic acids and their derivatives, polysaccharides, in particular Xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also fatty alcohols, Monoglycerides and fatty acids, polyacrylates, polyvinyl alcohol and Polyvinyl pyrrolidone. Biogenic active ingredients are, for example Plant extracts, protein hydrolyzates and vitamin complexes too understand. Common film formers are, for example, hydrocolloids such as chitosan, microcrystalline chitosan or quaternized Chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, Polymers of the acrylic acid series, quaternary Cellulose derivatives and similar compounds. As a preservative are suitable, for example, formaldehyde solution, p-hydroxybenzoate or sorbic acid. Examples of pearlescent agents are: Glycol distearic acid esters such as ethylene glycol distearate, however also fatty acids and fatty acid monoglycol esters into consideration. As dyes used in addition to the carotenoid aggregates can use those approved and approved for cosmetic purposes Substances are used, such as in the Publication "Cosmetic Dyes" of the Dye Coimmission the German Research Foundation, published by the publisher Chemie, Weinheim, 1984. These dyes are usually in a concentration of 0.001 to 0.1% by weight, based on the entire mixture used.
Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 80, vorzugsweise 6 bis 40 Gew.-% und der nicht wäßrige Anteil ("Aktivsubstanz") 20 bis 80, vorzugsweise 30 bis 70 Gew.-% bezogen auf die Gesamtmenge der Zubereitung - betragen. Die Herstellung der Zubereitung kann in an sich bekannter Weise, d.h. beispielsweise durch Heiß-, Kalt-, Heiß-Heiß/Kalt- bzw. PIT-Emulgierung erfolgen.The total proportion of auxiliaries and additives can be 1 to 80, preferably 6 to 40% by weight and the non-aqueous portion ("active substance") 20 to 80, preferably 30 to 70 wt .-% based on the total amount of preparation - amount. The manufacture of the Preparation can be carried out in a manner known per se, i.e. for example by hot, cold, hot-hot / cold or PIT emulsification.
Bevorzugte kosmetische oder pharmazeutische Zubereitungen sind beispielsweise transparente Formulierungen in Form durchsichtiger Emulsionen, Solubilisate, Gele oder alkoholisch-wäßriger Lotionen.Preferred cosmetic or pharmaceutical preparations are for example, transparent formulations in the form of more transparent Emulsions, solubilisates, gels or alcoholic-aqueous Lotions.
In den nachfolgenden Beispielen wird die erfindungsgemäße Verwendung der Carotinoid-Aggregate näher erläutert. In the following examples, the invention Use of the carotenoid aggregates explained in more detail.
Von einer molekularen Lösung von 50 mg Astaxanthin pro Liter Aceton wurden 5 ml mit 95 ml eines Gemisches aus 70 ml Wasser und 30 ml Aceton bei Raumtemperatur vermischt. Innerhalb von ca. 30 Minuten bildeten sich J-Aggregate, die durch einen Farbumschlag von orange nach rosa direkt sichtbar wurden. Bei 10 minütiger Bestrahlung dieser Aggregat-Lösung in einer Bestrahlungsapparatur (Suntest®, Fa. Heraeus) war keine Farbänderung zu beobachten. Wurde eine Vergleichslösung von molekular gelöstem Astaxanthin (2,5 ppm Astaxanthin in Aceton) unter gleichen Bedingungen bestrahlt, so war die Farbe nach 10 Minuten vollständig verschwunden.5 ml of a molecular solution of 50 mg of astaxanthin per liter of acetone were mixed with 95 ml of a mixture of 70 ml of water and 30 ml of acetone at room temperature. J-aggregates formed within approx. 30 minutes, which became directly visible through a color change from orange to pink. At 10 minutes of irradiation of this aggregate solution in an irradiation apparatus (sun test ®, Fa. Heraeus) no color change was observed. If a reference solution of molecularly dissolved astaxanthin (2.5 ppm astaxanthin in acetone) was irradiated under the same conditions, the color had completely disappeared after 10 minutes.
Anhand der vor und nach der Bestrahlung gemessenen UV/VisSpektren konnte die erhöhte Lichtstabilität der J-Aggregate von Astaxanthin gegenüber der monomeren Form verdeutlicht werden [siehe FIG. 1: (1) Astaxanthin Monomerform, vor der Bestrahlung; (2) Monomerform, nach der Bestrahlung; (3) Astaxanthin J-Aggregat, vor der Bestrahlung; (4) J-Aggregat, nach der Bestrahlung].Based on the UV / Vis spectra measured before and after the irradiation could the increased light stability of the J-aggregates of astaxanthin compared to the monomeric form become [see FIG. 1: (1) astaxanthin monomer form, before irradiation; (2) monomer form, after irradiation; (3) Astaxanthin J-aggregate, before irradiation; (4) J-aggregate, after irradiation].
Von einer molekularen Lösung von 50 mg Lycopin pro Liter Isopropanol wurden 5 ml mit 95 ml eines Gemisches aus 30 ml Wasser und 70 ml Isopropanol vermischt. Innerhalb von Sekunden bildeten sich H-Aggregate, die durch eine Farbverschiebung von orange nach gelb-orange direkt sichtbar wurden. Bei 10 minütiger Bestrahlung dieser Aggregat-Lösung in einer Bestrahlungsapparatur (Suntest®, Fa. Heraeus) war nur eine geringe Farbänderung zu beobachten. Die Bestrahlung einer Vergleichslösung von molekular gelöstem Lycopin (2,5 ppm Lycopin in Isopropanol) unter gleichen Bedingungen führte zu einer stärkeren Abnahme der Farbintensität. Durch Verdünnen und Erwärmen konnten die bestrahlten Lösungen in den molekular gelösten Zustand überführt und quantitativ analysiert werden. Das in der Lösung in Aggregatform vorliegende Lycopin war um den Faktor 1,5 stabiler als Lycopin in monomerer Form.From a molecular solution of 50 mg lycopene per liter of isopropanol were 5 ml with 95 ml of a mixture of 30 ml of water and 70 ml of isopropanol mixed. Formed within seconds H-aggregates, which are caused by a color shift from orange to yellow-orange were directly visible. With 10 minutes of radiation this aggregate solution in an irradiation apparatus (Suntest®, Heraeus) only a slight change in color was observed. The Irradiation of a reference solution of molecularly dissolved lycopene (2.5 ppm lycopene in isopropanol) under the same conditions led to a greater decrease in color intensity. By The irradiated solutions could be diluted and heated in the Molecularly dissolved state transferred and analyzed quantitatively become. The lycopene present in the solution in aggregate form was 1.5 times more stable than lycopene in monomeric form.
Claims (12)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19802134A DE19802134A1 (en) | 1998-01-21 | 1998-01-21 | Use of carotenoid aggregates as colorants |
| DE19802134 | 1998-01-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0930022A2 true EP0930022A2 (en) | 1999-07-21 |
| EP0930022A3 EP0930022A3 (en) | 2001-09-05 |
| EP0930022B1 EP0930022B1 (en) | 2003-09-17 |
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|---|---|---|---|
| EP98122311A Expired - Lifetime EP0930022B1 (en) | 1998-01-21 | 1998-11-24 | Use of carotinoid aggregates as colourants |
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| US (1) | US6827941B1 (en) |
| EP (1) | EP0930022B1 (en) |
| JP (1) | JP3921305B2 (en) |
| CN (1) | CN1121153C (en) |
| CA (1) | CA2257552C (en) |
| DE (2) | DE19802134A1 (en) |
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| EP1957035A1 (en) * | 2005-12-09 | 2008-08-20 | The Procter and Gamble Company | Personal care compositions |
| WO2009080572A1 (en) * | 2007-12-21 | 2009-07-02 | Unilever Plc | Topical composition comprising coloring antioxidants |
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| DE20109224U1 (en) * | 2001-06-01 | 2002-10-17 | Dr. Marcus GmbH & Co. KG, 21502 Geesthacht | Dye mixture for food, pharmaceuticals and cosmetics |
| US7375133B2 (en) * | 2002-07-29 | 2008-05-20 | Cardax Pharmaceuticals, Inc. | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| US7723327B2 (en) * | 2002-07-29 | 2010-05-25 | Cardax Pharmaceuticals, Inc. | Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease |
| EP1532108B1 (en) * | 2002-07-29 | 2016-06-29 | Cardax Pharma, Inc. | Astaxanthin esters for the inhibition and amelioration of disease |
| US7345091B2 (en) * | 2002-07-29 | 2008-03-18 | Cardax Pharmaceuticals, Inc. | Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| JP2005002175A (en) * | 2003-06-10 | 2005-01-06 | Toyo Koso Kagaku Kk | Packaged astaxanthin-containing liquid soap and rinse |
| JP4562174B2 (en) * | 2004-08-23 | 2010-10-13 | カゴメ株式会社 | Method for producing carotenoid-containing material |
| US20060111580A1 (en) * | 2004-10-01 | 2006-05-25 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids |
| WO2007020057A1 (en) * | 2005-08-15 | 2007-02-22 | Phares Pharmaceutical Research N.V. | Crystal forms of astaxanthin |
| WO2007091779A1 (en) | 2006-02-10 | 2007-08-16 | Lg Electronics Inc. | Digital broadcasting receiver and method of processing data |
| WO2007126196A1 (en) | 2006-04-29 | 2007-11-08 | Lg Electronics Inc. | Digital broadcasting system and method of processing data |
| WO2007136166A1 (en) | 2006-05-23 | 2007-11-29 | Lg Electronics Inc. | Digital broadcasting system and method of processing data |
| US7873104B2 (en) | 2006-10-12 | 2011-01-18 | Lg Electronics Inc. | Digital television transmitting system and receiving system and method of processing broadcasting data |
| ATE501644T1 (en) * | 2007-01-16 | 2011-04-15 | Basf Se | LIQUID FORMULATIONS CONTAINING CAROTINOIDS |
| KR101253185B1 (en) | 2007-03-26 | 2013-04-10 | 엘지전자 주식회사 | Digital broadcasting system and data processing method |
| KR101285887B1 (en) | 2007-03-26 | 2013-07-11 | 엘지전자 주식회사 | Digital broadcasting system and method of processing data in digital broadcasting system |
| KR101285888B1 (en) | 2007-03-30 | 2013-07-11 | 엘지전자 주식회사 | Digital broadcasting system and method of processing data in digital broadcasting system |
| WO2009005326A2 (en) | 2007-07-04 | 2009-01-08 | Lg Electronics Inc. | Digital broadcasting system and method of processing data |
| US8433973B2 (en) * | 2007-07-04 | 2013-04-30 | Lg Electronics Inc. | Digital broadcasting system and method of processing data |
| KR20090012180A (en) | 2007-07-28 | 2009-02-02 | 엘지전자 주식회사 | Digital broadcasting system and method of processing data in digital broadcasting system |
| CN101836448A (en) | 2007-08-24 | 2010-09-15 | Lg电子株式会社 | Digital broadcasting system and method of processing data in digital broadcasting system |
| JP2013199466A (en) | 2012-02-24 | 2013-10-03 | Fujifilm Corp | Lycopene-containing composition |
| JP5280571B1 (en) * | 2012-08-20 | 2013-09-04 | 株式会社タイショーテクノス | Liquid pigment preparation for food and method for producing processed food using the same |
| JP6426902B2 (en) * | 2014-03-20 | 2018-11-21 | 株式会社コーセー | Carotenoid-Containing Composition, Carotenoid Deterioration Inhibitor, and Carotenoid Deterioration Suppression Method |
| US10479906B2 (en) * | 2015-09-18 | 2019-11-19 | Oregon State University | Use of fungal pigments from wood-staining fungi as colorants in wood finishes and paints |
| JP7128739B2 (en) * | 2016-04-01 | 2022-08-31 | 三栄源エフ・エフ・アイ株式会社 | Method for stabilizing solid dyes |
| WO2020112524A1 (en) * | 2018-11-29 | 2020-06-04 | Sevanti Mehta | Manufacture of carotenoid compositions |
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| JPH0762116B2 (en) * | 1986-12-06 | 1995-07-05 | 丸善製薬株式会社 | Carotenoid pigment composition |
| JP3727077B2 (en) * | 1994-09-27 | 2005-12-14 | 新日本石油株式会社 | Extraction method of carotenoid compounds from bacterial cells |
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- 1998-11-24 DE DE59809639T patent/DE59809639D1/en not_active Expired - Lifetime
-
1999
- 1999-01-07 US US09/226,143 patent/US6827941B1/en not_active Expired - Lifetime
- 1999-01-14 CA CA002257552A patent/CA2257552C/en not_active Expired - Lifetime
- 1999-01-19 JP JP01040199A patent/JP3921305B2/en not_active Expired - Lifetime
- 1999-01-21 CN CN99101364A patent/CN1121153C/en not_active Expired - Lifetime
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1957035A1 (en) * | 2005-12-09 | 2008-08-20 | The Procter and Gamble Company | Personal care compositions |
| WO2009080572A1 (en) * | 2007-12-21 | 2009-07-02 | Unilever Plc | Topical composition comprising coloring antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19802134A1 (en) | 1999-07-22 |
| JP3921305B2 (en) | 2007-05-30 |
| DE59809639D1 (en) | 2003-10-23 |
| JPH11285359A (en) | 1999-10-19 |
| CN1228937A (en) | 1999-09-22 |
| EP0930022B1 (en) | 2003-09-17 |
| CA2257552A1 (en) | 1999-07-21 |
| US6827941B1 (en) | 2004-12-07 |
| CA2257552C (en) | 2007-10-30 |
| CN1121153C (en) | 2003-09-17 |
| EP0930022A3 (en) | 2001-09-05 |
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